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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-08-16 03:38:18 UTC
Secondary Accession Numbers
  • HMDB01198
  • HMDB06015
Metabolite Identification
Common NameLeukotriene C4
DescriptionLeukotriene C4 (LTC4) is a cysteinyl leukotriene (CysLT), a family of potent inflammatory mediators. Eosinophils, one of the principal cell types recruited to and activated at sites of allergic inflammation, is capable of elaborating lipid mediators, including leukotrienes derived from the oxidative metabolism of arachidonic acid (AA). Potentially 'activated' eosinophils may elaborate greater quantities of LTC4, than normal eosinophils. These activated eosinophils thus are 'primed' for enhanced LTC4 generation in response to subsequent stimuli. Some recognized priming stimuli are chemoattractants (e.g., eotaxin, PAF) that may participate in the recruitment of eosinophils to sites of allergic inflammation. The mechanisms by which chemoattractants and other activating cytokines (e.g., interleukin (IL)-5) or extracellular matrix components (e.g., fibronectin) enhance eosinophil eicosanoid formation are pertinent to the functions of these eicosanoids as paracrine mediators of allergic inflammation. Some eosinophil-derived eicosanoids may be active in down-regulating inflammation. It is increasingly likely that eicosanoids synthesized within cells, including eosinophils, may have intracellular (e.g., intracrine) roles in regulating cell functions, in addition to the more recognized activities of eicosanoids as paracrine mediators of inflammation. Acting extracellularly, the cysteinyl leukotrienes (CysLTs) LTC4 and its extracellular derivatives, LTD4 and LTE4 are key paracrine mediators pertinent to asthma and allergic diseases. Based on their receptor-mediated capabilities, they can elicit bronchoconstriction, mucous hypersecretion, bronchial hyperresponsiveness, increased microvascular permeability, and additional eosinophil infiltration. Eosinophils are a major source of CysLTs and have been identified as the principal LTC4 synthase expressing cells in bronchial mucosal biopsies of asthmatic subjects. (PMID: 12895596 )Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways.
5S,6R-LTC(Sub 4)ChEBI
5S-Hydroxy,6R-(S-glutathionyl),7E,9E,11Z,14Z-eicosatetraenoic acidChEBI
LTC (Sub 4)ChEBI
Leucotriene C4HMDB
Leukotriene CHMDB
Leukotriene C1HMDB
[R-[R*,s*-(e,e,Z,Z)]]-N-[S-[1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl]-N-L-gamma-glutamyl-L-cysteinyl]-glycine 5S,6R-LTC4HMDB
Leukotriene C-4MeSH
Leukotriene C-1MeSH
Leukotrienes CMeSH
Leukotriene C 1MeSH
Leukotriene C 4MeSH
Chemical FormulaC30H47N3O9S
Average Molecular Weight625.774
Monoisotopic Molecular Weight625.303300807
IUPAC Name(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid
Traditional Nameleukotriene C4
CAS Registry Number72025-60-6
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentOligopeptides
Alternative Parents
  • Alpha-oligopeptide
  • Gamma-glutamyl alpha peptide
  • Leukotriene
  • Hydroxyeicosatetraenoic acid
  • Eicosanoid
  • Glutamine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Cysteine or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Alpha-amino acid
  • N-substituted-alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Hydroxy fatty acid
  • Thia fatty acid
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Secondary alcohol
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Dialkylthioether
  • Carboxylic acid
  • Sulfenyl compound
  • Thioether
  • Primary amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
StatusDetected and Quantified
  • Endogenous
  • Component of Prostaglandin and leukotriene metabolism
ApplicationNot Available
Cellular locations
  • Extracellular
  • Endoplasmic reticulum
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.0025 mg/mLALOGPS
pKa (Strongest Acidic)1.8ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area216.35 Å2ChemAxon
Rotatable Bond Count25ChemAxon
Refractivity168.51 m3·mol-1ChemAxon
Polarizability68.38 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • Intestine
  • Lens
  • Leukocyte
  • Neutrophil
  • Platelet
  • Skin
  • Smooth Muscle
Acetaminophen Action PathwaySMP00710Not Available
Acetylsalicylic Acid PathwaySMP00083Not Available
Antipyrine Action PathwaySMP00692Not Available
Antrafenine Action PathwaySMP00693Not Available
Arachidonic Acid MetabolismSMP00075map00590
Bromfenac PathwaySMP00102Not Available
Carprofen Action PathwaySMP00694Not Available
Celecoxib PathwaySMP00096Not Available
Diclofenac PathwaySMP00093Not Available
Diflunisal PathwaySMP00289Not Available
Etodolac PathwaySMP00084Not Available
Etoricoxib Action PathwaySMP00695Not Available
Fc Epsilon Receptor I Signaling in Mast CellsSMP00358Not Available
Fenoprofen Action PathwaySMP00696Not Available
Flurbiprofen Action PathwaySMP00697Not Available
Ibuprofen PathwaySMP00086Not Available
Indomethacin PathwaySMP00104Not Available
Ketoprofen PathwaySMP00085Not Available
Ketorolac PathwaySMP00098Not Available
Leukotriene C4 Synthesis DeficiencySMP00353Not Available
Lornoxicam Action PathwaySMP00700Not Available
Lumiracoxib Action PathwaySMP00699Not Available
Magnesium salicylate Action PathwaySMP00698Not Available
Mefanamic Acid PathwaySMP00109Not Available
Meloxicam PathwaySMP00106Not Available
Nabumetone PathwaySMP00114Not Available
Naproxen PathwaySMP00120Not Available
Nepafenac Action PathwaySMP00702Not Available
Oxaprozin PathwaySMP00113Not Available
Phenylbutazone Action PathwaySMP00701Not Available
Piroxicam PathwaySMP00077Not Available
Rofecoxib PathwaySMP00087Not Available
Salicylate-sodium Action PathwaySMP00708Not Available
Salicylic Acid Action PathwaySMP00709Not Available
Salsalate Action PathwaySMP00707Not Available
Sulindac PathwaySMP00094Not Available
Suprofen PathwaySMP00101Not Available
Tenoxicam Action PathwaySMP00706Not Available
Tiaprofenic Acid Action PathwaySMP00705Not Available
Tolmetin Action PathwaySMP00704Not Available
Trisalicylate-choline Action PathwaySMP00703Not Available
Valdecoxib PathwaySMP00116Not Available
Normal Concentrations
BloodDetected and Quantified4.7E-5 +/- 2.3E-5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.001359 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00006 +/- 0.00003 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified6.989e-05 +/- 2.767e-05 uMNot SpecifiedNot SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000133 +/- 3.454e-05 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000101 uMNot SpecifiedNot SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified7.996e-05 uMNot SpecifiedNot SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified1.791e-05 +/- 4.798e-06 uMNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
BloodDetected and Quantified0.00024 +/- 0.000065 uMAdult (>18 years old)BothEczema details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000153 +/- 1.711e-05 uMAdult (>18 years old)Not SpecifiedSpinal cord injuries (acute stage) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000557 uMNot SpecifiedNot SpecifiedAIDS details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000185 +/- 7.628e-05 uMChildren (1-13 years old)Not SpecifiedAseptic meningitis details
Cerebrospinal Fluid (CSF)Detected and Quantified<7.996e-05 uMNot SpecifiedNot Specifiedclosed head injury details
Cerebrospinal Fluid (CSF)Detected and Quantified1.343e-05 uMAdult (>18 years old)Maleglutathione synthetase deficiency, acute metabolic crisis details
Cerebrospinal Fluid (CSF)Detected and Quantified<7.996e-05 uMNot SpecifiedNot Specifiedgunshot wound details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000422 uMNot SpecifiedNot SpecifiedHIV-Seropositive details
Cerebrospinal Fluid (CSF)Detected and Quantified2.399e-05 uMNot SpecifiedNot SpecifiedHIV-Seropositive, Dementia details
Cerebrospinal Fluid (CSF)Detected and Quantified<0.000160 uMNot SpecifiedNot Specifiedhydrocephalus details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00413 +/- 0.000611 uMNot SpecifiedNot Specifiedsubarachnoid hemorrhage with cerebral vasospasm details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000280 uMNot SpecifiedNot SpecifiedHIV-Seropositive (Neurologically normal) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00130 +/- 0.000227 uMNot SpecifiedNot Specifiedsubarachnoid hemorrhage without cerebral vasospasm details
Associated Disorders and Diseases
Disease References
  1. Hua Z, Fei H, Mingming X: Evaluation and interference of serum and skin lesion levels of leukotrienes in patients with eczema. Prostaglandins Leukot Essent Fatty Acids. 2006 Jul;75(1):51-5. Epub 2006 Jun 6. [PubMed:16757158 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022484
KNApSAcK IDNot Available
Chemspider ID4444133
KEGG Compound IDC02166
BiGG ID2212273
Wikipedia LinkLeukotriene C4
NuGOwiki LinkHMDB0001198
PubChem Compound5280493
PDB IDNot Available
ChEBI ID16978
Synthesis ReferenceRokach, Joshua; Young, Robert N.; Kakushima, Masatoshi; Lau, Cheuk-Kun; Seguin, Rick; Frenette, Richard; Guindon, Yvan. Synthesis of leukotrienes. New synthesis of natural leukotriene A4. Tetrahedron Letters (1981), 22(11), 979-82.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sjolinder M, Tornhamre S, Claesson HE, Hydman J, Lindgren J: Characterization of a leukotriene C4 export mechanism in human platelets: possible involvement of multidrug resistance-associated protein 1. J Lipid Res. 1999 Mar;40(3):439-46. [PubMed:10064732 ]
  2. Chen ZS, Guo Y, Belinsky MG, Kotova E, Kruh GD: Transport of bile acids, sulfated steroids, estradiol 17-beta-D-glucuronide, and leukotriene C4 by human multidrug resistance protein 8 (ABCC11). Mol Pharmacol. 2005 Feb;67(2):545-57. Epub 2004 Nov 10. [PubMed:15537867 ]
  3. Lane SJ, Lee TH: Mast cell effector mechanisms. J Allergy Clin Immunol. 1996 Nov;98(5 Pt 2):S67-71; discussion S71-2. [PubMed:8939179 ]
  4. Sawazaki Y: [Leukotriene B4, leukotriene C4 and prostaglandin E2 in the serum, synovial fluid and synovium in patients with rheumatoid arthritis]. Nihon Ika Daigaku Zasshi. 1989 Dec;56(6):559-64. [PubMed:2558123 ]
  5. Heimburger M, Palmblad JE: Effects of leukotriene C4 and D4, histamine and bradykinin on cytosolic calcium concentrations and adhesiveness of endothelial cells and neutrophils. Clin Exp Immunol. 1996 Mar;103(3):454-60. [PubMed:8608646 ]
  6. Romero R, Wu YK, Mazor M, Hobbins JC, Mitchell MD: Increased amniotic fluid leukotriene C4 concentration in term human parturition. Am J Obstet Gynecol. 1988 Sep;159(3):655-7. [PubMed:3421265 ]
  7. Paoletti P, Gaetani P, Grignani G, Pacchiarini L, Silvani V, Rodriguez y Baena R: CSF leukotriene C4 following subarachnoid hemorrhage. J Neurosurg. 1988 Oct;69(4):488-93. [PubMed:3418380 ]
  8. De Servi S, Ricevuti G, Mazzone A, Pasotti D, Bramucci E, Angoli L, Specchia G: Transcardiac release of leukotriene C4 by neutrophils in patients with coronary artery disease. J Am Coll Cardiol. 1991 Apr;17(5):1125-8. [PubMed:2007712 ]
  9. Koshino T, Takano S, Houjo T, Sano Y, Kudo K, Kihara H, Kitani S, Takaishi T, Hirai K, Ito K, Morita Y: Expression of 5-lipoxygenase and 5-lipoxygenase-activating protein mRNAs in the peripheral blood leukocytes of asthmatics. Biochem Biophys Res Commun. 1998 Jun 18;247(2):510-3. [PubMed:9642160 ]
  10. Richter L, Hesselbarth N, Eitner K, Schubert K, Bosseckert H, Krell H: Increased biliary secretion of cysteinyl-leukotrienes in human bile duct obstruction. J Hepatol. 1996 Nov;25(5):725-32. [PubMed:8938552 ]
  11. Sternfeld M, Fink A, Bentwich Z, Eliraz A: The role of acupuncture in asthma: changes in airways dynamics and LTC4 induced LAI. Am J Chin Med. 1989;17(3-4):129-34. [PubMed:2633615 ]
  12. Ponicke K, Forster W: Influence of leukotriene C4 on aggregation and on malondialdehyde formation of human blood platelets. Biomed Biochim Acta. 1984;43(8-9):S459-62. [PubMed:6440558 ]
  13. Angi MR, Bettero A, Filippi F, Salvalaio L, Benassi CA: [Quantitative evaluation of conjunctival irritation by simultaneous determination of histamine, serotonin and leukotriene C4 in tears]. Ophtalmologie. 1987 Oct-Dec;1(4):509-11. [PubMed:3153930 ]
  14. Cruz JR, Cano F, Razin E, Acheson DW, Keusch GT: Fecal excretion of leukotriene C4 during human disease due to Shigella dysenteriae. J Pediatr Gastroenterol Nutr. 1995 Feb;20(2):179-83. [PubMed:7714683 ]
  15. Zijlstra FJ, Wilson JH: 15-HETE is the main eicosanoid present in mucus of ulcerative proctocolitis. Prostaglandins Leukot Essent Fatty Acids. 1991 May;43(1):55-9. [PubMed:1652771 ]
  16. Matsumoto S, Hayashi Y, Kinoshita I, Ikata T, Yamamoto S: Immunoaffinity purification of prostaglandin E2 and leukotriene C4 prior to radioimmunoassay: application to human synovial fluid. Ann Clin Biochem. 1993 Jan;30 ( Pt 1):60-8. [PubMed:8434868 ]
  17. Talbot SF, Atkins PC, Goetzl EJ, Zweiman B: Accumulation of leukotriene C4 and histamine in human allergic skin reactions. J Clin Invest. 1985 Aug;76(2):650-6. [PubMed:2411760 ]
  18. Kloprogge E, de Leeuw AJ, de Monchy JG, Kauffman HF: Cellular communication in leukotriene C4 production between eosinophils and neutrophils. Int Arch Allergy Appl Immunol. 1989;90(1):20-3. [PubMed:2509375 ]
  19. Damtew B, Spagnuolo PJ: Leukotriene C4 from vascular endothelium enhances neutrophil adhesiveness. Prostaglandins Leukot Essent Fatty Acids. 1997 Feb;56(2):111-6. [PubMed:9051719 ]
  20. Schauer U, Eckhart A, Muller R, Gemsa D, Rieger CH: Enhanced leukotriene C4 production by peripheral eosinophilic granulocytes from children with asthma. Int Arch Allergy Appl Immunol. 1989;90(3):201-6. [PubMed:2512259 ]
  21. Bandeira-Melo C, Weller PF: Eosinophils and cysteinyl leukotrienes. Prostaglandins Leukot Essent Fatty Acids. 2003 Aug-Sep;69(2-3):135-43. [PubMed:12895596 ]


General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Initiates extracellular glutathione (GSH) breakdown, provides cells with a local cysteine supply and contributes to maintain intracellular GSH level. It is part of the cell antioxidant defense mechanism. Catalyzes the transfer of the glutamyl moiety of glutathione to amino acids and dipeptide acceptors. Alternatively, glutathione can be hydrolyzed to give Cys-Gly and gamma glutamate. Isoform 3 seems to be inactive.
Gene Name:
Uniprot ID:
Molecular weight:
Leukotriene C4 + Amino acid → Leukotriene D4 + 5-L-Glutamyl amino aciddetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves glutathione conjugates (By similarity).
Gene Name:
Uniprot ID:
Molecular weight:
Leukotriene C4 + Amino acid → Leukotriene D4 + 5-L-Glutamyl amino aciddetails
General function:
Involved in enzyme activator activity
Specific function:
Catalyzes the conjugation of leukotriene A4 with reduced glutathione to form leukotriene C4.
Gene Name:
Uniprot ID:
Molecular weight:
Leukotriene A4 + Glutathione → Leukotriene C4details
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves glutathione conjugates (By similarity).
Gene Name:
Uniprot ID:
Molecular weight:
Leukotriene C4 + Amino acid → Leukotriene D4 + 5-L-Glutamyl amino aciddetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves the gamma-glutamyl peptide bond of glutathione conjugates, but maybe not glutathione itself. Converts leukotriene C4 (LTC4) to leukotriene D4 (LTD4).
Gene Name:
Uniprot ID:
Molecular weight:
Leukotriene C4 + Amino acid → Leukotriene D4 + 5-L-Glutamyl amino aciddetails


General function:
Involved in ATP binding
Specific function:
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:
Uniprot ID:
Molecular weight: